Fear, it always seemed to be a part of his life. Fear was the feeling coursing through Tyler Croft at this moment as he entered the hotel and headed to the small bar just off the lobby. The initial excitement he had felt upon his arrival had faded and the fear returned.
He felt eyes on the movement of his butt under his leather miniskirt he entered the bar and located an unoccupied booth. The seat and back cushions were soft and the interior was warm, cozy, and richly appointed and he began to relax. A waitress appeared and took his drink order as he continued to settle in. He crossed his legs in an attempt to get comfortable and momentarily forgot the fear as he admired the look of them under the black nylons stockings, they looked great. He then smoothed the front of the short skirt in a practiced gesture to banish any wrinkles.
He sat back against the cushions and started playing the if-only game. If only he had not started chatting with the male on that site. If only he had ignored the requests to post some pictures, but he didn't. How his head reeled at the comments those pictures received, not only from him but some of the others on the site. If only he had not been so weak.
" What were you thinking," Tyler said to himself as he glanced around the room. " This was never about appearing in public."
For so many years he had worked hard to kept this part of his life a secret, fear of discovery was a great motivator. Now here he was out in public for all to see.
It started when he was much younger and it began with felching a few items from his sister's room and wearing them behind closed doors. Like many, he had no idea where his desire came from, and instead of ignoring it, he obeyed it. Until that day he was a typical teenage male and did the things most males his age, they did not include having a desire to wear his sister's panties.
He recalled trembling with anticipation as he removed his outer clothing and underwear and then reached for the items that he had borrowed. Oh, how his cock began to tingle and thicken the first time he stepped into a pair of his sister's silk panties and began to slowly draw them up his legs. The sensation of his raging erection and balls being held in place by the tiny silky cocoon was beyond description.
His body tingled again as he fastened the blue silk and lace bra around his chest and ran both hands over the silky bra cups. He was a little depressed that he had nothing to fill the cups but it didn't last long. Recalling what he had heard in high school he began carefully stuffing the empty bra cups with kleenex. It gave him the look and feel of breasts and more than once he emptied his load in his tiny panties as he ran his hands over the full and silky bra cups.
The fear of discovery was always present and he did his best to overcome it. He made sure that his bedroom door was always locked and even leaned a chair against the doorknob and that he only dressed in the wee hours of the morning when everyone in the house was fast asleep.
Even on those occasions when his parents were out for the evening he still practiced this level of protection in case his sister came home early. Not that she was in the habit of opening the door to his room without knocking but better safe than sorry. He would have a difficult time explaining why he was wearing her lingerie.
Eventually, his sister's lingerie was not enough and he began to borrow skirts, blouses, and pantyhose. His sister was a clothing junkie and there were racks of her old clothing hanging in the basement many of which had been earmarked for charitable donations so they would not be missed. As he and his sister were twins they shared a similar body type so her clothing fit him very well.
Tyler soon lost track of the number of nights that he flopped onto his bed once fully dressed in the borrowed finery and ran his hands over his body as his teenage cock became harder with each passing minute. As usual, one hand ended up sliding under his skirt and along his pantyhose covered legs until it reached his crotch. Once there he allowed his fingertips to run over the bulge his cock made under his silky lingerie and almost immediately lost his load in his silk panties.
While he was quite happy with the way his body looked and felt he was saddened that his face still looked like a male. That's when he became interested in makeup, but there were no resources to obtain that information. He didn't dare talk to his sister as that would have raised suspicion and the family only had one desktop and he was sure that his parents kept track of the sites he and his sister visited. It was the gift of a laptop from his parents to him and his sister that Christmas that had changed everything.
"Just don't visit too many porno sites," his Dad joked even as his Mom smacked him for making such a comment.
He remembers telling his parents not to worry as he wasn't into porn and that was the truth. He began to visit sites that offered makeup and makeup instructions. He remembered taking money from his savings account and placing an order for the products that these sites recommended. He had the package delivered to his Grandmother's house as the fear of discovery still loomed and he knew that Grandma wouldn't question it.
He practiced applying makeup every chance he got and over the years he became quite proficient at it. He remembered the fear of being seen with traces of makeup on his face and always took an extra amount of time when removing it. He moved out of his parents shortly after graduation into a beautiful condo as he had landed a well-paid entry-level position as an IT. Now he was free to order whatever he wanted without the fear of detection, and order he did.
Soon nighties, garter belts, and nylons filled his dresser drawers along with a collection of the silkiest panties he could find along with their matching bras. He discovered breast inserts and ordered a half a dozen different styles. His closet held a collection of short skirts and blouses along with high heels and a few long brunette wigs.
A large three-sided mirror similar to what you find in department stores graced one corner of his ready room and he spent hours admiring himself once full made up and dressed.
"Maybe you should have been born a girl," he often said to the reflection of the pretty girl in the mirror's surface.
He taught himself to walk in the highest of high heels across any surface for reasons he didn't understand as he wasn't about to go out in public dressed up. When the option to work from home became available he seized it and was able to perform his tasks while dressed and made up.
Everything changed when he discovered Lush Stories and created an account. He spent hours reading and commenting on the stories and even responded to a friend request from a male that called himself the midnight lover. Tyler soon found himself chatting with him almost every day and was surprised to learn that they lived in the same state and only a few cities away. Cell phone numbers were exchanged and their daily talks became easier and more enjoyable.
It was at his newfound friend's suggestion that he post a few pictures of himself all made up once he had admitted to his secret passion and the reaction he received was something he didn't count on.
"Damn, you are one sexy looking lady and I would give anything to meet you in person," he stated.
Tyler politely declined the invite and his friend didn't bring it up again for quite a while. It was after Tyler posted a picture of himself in a black leather miniskirt, black blouse, and black nylons that he asked again and this time for some unknown reason Tyler agreed. A place, time, and date were decided and agreed upon
More than once Tyler had the urge to cancel the meeting because his friend didn't post any pics of himself and he worried that this could be some overweight and a hairy lump of a male. Tyler was assured a dozen times by his unseen friend that he was considered quite handsome and in pretty good shape and didn't post any pics as he also feared detection.
It was just a little shy of four o'clock that he spied the tall and tanned male with a headful of silver hair and clad in a great looking suit enter the bar and scan the interior. A second later he headed to where Tyler was seated.
"Tia?" he asked when he stood next to her booth.
Tia was the name he used when fully made up.
"Yes," the brunette responded as he stared into the handsome face of this male.
"I'm the midnight lover or you can call me Vince," he responded with a smile as he slid into the booth opposite of Tyler.
They both stared at each other for the longest time. Tyler thought him to be one of the most handsome men he had ever seen and Vince admitted that he had never met a female that looked as good as Tyler. Over drinks they began to talk about their lives and the choices they had made and Tyler felt he had found a kindred spirit and the fear vanished.
During the hour of conversation that followed Vince slid around and so did Tyler. Soon they were sitting next to each other in the center of the booth. He complimented him on how sexy his outfit was and how his legs looked. Tyler blushed at these compliments. Eventually, Vince took hold of Tyler's hands that were resting on the table.
"I took the liberty of getting a room if you're inclined to get out of here," he said in a quiet voice.
Tyler felt his cock begin to tingle in their silken cocoon and his man nipples harden under the phony breasts at the mention of a room and once again the fear returned. Was he ready to take such a step? Looking like a female was one thing but performing as one behind closed doors with another male was something else.
"I don't know if that's such a good idea. How do I know that once behind closed doors you won't throw me on the bed and take me against my will?" Tyler said softly in a female voice that he didn't know he possessed.
"I would never do that, " Vince responded in a voice as smooth as silk and Tyler believed him.
They left together and slowly walked the carpeted hallway to the room Vince had secured. Once inside Tyler took a seat on the small couch as Vince fixed drinks. He deposited the beverages and then took a seat on the other end. When there was a lull in the conversation Tyler asked his friend if everything was all right.
"Yes, it is. I'm just being overwhelmed by the desire to kiss your red lips," he admitted in a shy voice.
Once again the fear reappeared. This good looking older male admitted that he wanted to kiss him and Tyler found himself wondering if he was ready for that. He had been kissed many times in high school and all the girls told him that he was a great kisser, but was he ready to kiss another male.
"I won't stop you if you tried," was all Tyler responded in his newly found feminine voice.
Vince slid next to Tyler and placed one arm across his slender shoulders and used his free hand to turn Tyler's pretty face in his direction. Vince then slowly moved his face closer to Tyler's and placed his lips on the moist red lips that he had been staring at for so long and gave them a quick close-mouthed kiss.
The contact sent a spark through both of their bodies and they just stared into each other's eyes afterward. The second kiss was held a little longer and Tyler responded by turning her body into Vince's and wrapping her arms around him and pressing her boobs into his chest. On the third kiss, Vince parted his lips and so did Tyler and allowed their tongues to touch.
"Oh, baby what you do to me," Vince stated when the kiss ended.
Tyler smiled at his statement because he too had been affected. His cock was hard and pushing against the silk of his panties and the leather of his miniskirt. He glanced over at Vince's lap and could see the bulge in his perfectly tailored slacks.
To Be Continued.
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